Democratic operative Tara McGowan is denying that her high-profile liberal firm ACRONYM played a role in the Monday evening caucus debacle, claiming that her firm was merely an investor in the company Shadow Inc., which developed the app at the center of the controversy. But internal company documents, a source close to the firms, and public records show a close and intertwined relationship between Acronym and Shadow.

In addition, ahead of the caucuses, questions swirled inside Shadow over the company’s ability to deliver a quality product, and there was concern from at least one staff member that senior leaders of Shadow and Acronym — both of which were launchedas a new Democratic bulwark against President Donald Trump — have been far from neutral in the Democratic primary.

Throughout the caucus yesterday, Democratic officials reported widespread problems downloading the app and inconsistencies uploading caucus results, leading to the Iowa Democratic Party’s decision to take the unusual step of delaying the release of the results. This is the first year the app was used, and ahead of the caucuses, the Iowa Democratic Party asked that the app’s name be kept secret. The New York Times reported that “its creators had repeatedly questioned the need to keep it secret.”

Kyle Tharp, a spokesperson for Acronym, released a statement on Monday night downplaying his company’s affiliation with Shadow.

“ACRONYM is an investor in several for-profit companies across the progressive media and technology sectors,” Tharp said. “One of those independent, for-profit companies is Shadow, Inc, which also has other private investors.”

David Plouffe, a former campaign manager to Barack Obama’s 2008 presidential bid who joined Acronym’s board, also distanced himself from the company during an MSNBC panel last night. “I have no knowledge of Shadow,” said Plouffe. “It was news to me.”

But previous statements and internal Acronym documents suggest that the two companies, which share office space in Denver, Colorado, are deeply intertwined.

Last year, McGowan, a co-founder of Acronym, wrote on Twitterthat she was “so excited to announce @anotheracronym has acquired Groundbase,” a firm that included “their incredible team led by [Gerard Niemira] + are launching Shadow, a new tech company to build smarter infrastructure for campaigns.” McGowan also noted that “With Shadow, we’re building a new model incentivized by adoption over growth.” The acquisition was announced in mid-January of last year.

In an interview on a related podcast last month, McGowan described Niemira as “the CEO of Shadow, which is the technology company that Acronym is the sole investor in now.”

What’s more, internal documents from Acronym show a close relationship with Shadow. An internal organizational chart shows digital strategy firm Lockwood Strategy, FWIW Media, and Shadow as part of a unified structure, with Acronym staff involved in the trio’s operations.

In an all-staff email sent last Friday, an official with Lockwood Strategy reminded team members about “COOL THINGS HAPPENING AROUND ACRONYM.” The list included bullets points such as, “The Iowa caucus is on Monday, and the Shadow team is hard at work,” and “Shadow is working on scaling up VAN integration with Shadow Messaging for some Iowa caucus clients.” (VAN refers to the widely used Democratic voter file technology firm.) Acronym staffers also attended the Shadow staff retreat.

A person with knowledge of the company’s culture, who asked to remain anonymous for fear of reprisal, shared communications showing that top officials at the company regularly expressed hostility to Sen. Bernie Sanders’s supporters. McGowan is married to Michael Halle, a senior strategist with the Buttigieg campaign. There is no evidence any preference of candidates had any effect on the coding issue that is stalling the Iowa results.

The Iowa Democratic Party and the Nevada Democratic Party retained Shadow to develop its caucus app. Shadow has also been retained for digital services by Buttigieg’s and Biden’s campaigns.

Acronym launched with a promise to compete with the Trump campaign’s strong emphasis on digital media, launching Democratic messages through paid advertisements on Facebook and other platforms. But the source said the company in many ways was woefully unprepared for the many challenges it had taken on, including the Iowa caucus app.

A precinct captain for Sanders, who requested anonymity because they were not authorized to talk to the press, confirmed that the rollout was rushed. “We didn’t know about the app until like a month ago. And we didn’t have access to the app until like three days ago,” the source said.

“This app has never been used in any real election or tested at a statewide scale and it’s only been contemplated for use for two months now,” David Jefferson, who also serves on the board of Verified Voting, a nonpartisan election integrity organization, told the New York Times.

Federal campaign finance records show that the Iowa Democratic Party and the Nevada Democratic Party retained Shadow to develop its caucus app. Shadow has also been retained for digital services by Buttigieg’s campaign, which paid the company $42,500 for software-related services last July, and by Joe Biden’s campaign, which paid Shadow $1,225 for text messaging services, last July as well.

Shadow was launched by former staffers to Hillary Clinton’s 2016 presidential campaign, including Niemira, Krista Davis, Ahna Rao, and James Hickey, according to professional biographies listed on LinkedIn. Shadow did not respond to a request for comment.

Acronym, which includes a hybrid model of a 501(c)4 entity that does not disclose donors and a Super PAC that does, has been a favorite for deep-pocketed Democratic donors. Donald Sussman, the founder of Paloma Partners, and Michael Moritz, a partner at Sequoia Capital, each donated $1 million to Acronym last year. Filmmaker Steven Spielberg gave $500,000. Investor Seth Klarman, once a major donor to Republican causes, gave $1.5 million to Acronym.

Acronym appears to have deleted portions of its website showcasing its involvement in Shadow. “ACRONYM is thrilled to announce the launch of Shadow, a new technology company that will exist under the ACRONYM umbrella and build accessible technological infrastructure and tools to enable campaigns to better harness, integrate and manage data across the platforms and technologies they all use,” wrote Niemira in a now-deleted blog post.

This morning, William McCurdy II, the chair of the Nevada Democratic Party, released a statement announcing that the party will not be using the Shadow app for its February caucus.

“NV Dems can confidently say that what happened in the Iowa caucus last night will not happen in Nevada on February 22nd. We will not be employing the same app or vendor used in the Iowa caucus,” said McCurdy. “We had already developed a series of backups and redundant reporting systems, and are currently evaluating the best path forward.”

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